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Senior Underwriter - Commercial Lines Auto

Remote / Online - Candidates ideally in
Toronto, Ontario, C6A, Canada
Listing for: Wawanesa Insurance
Full Time, Part Time, Remote/Work from Home position
Listed on 2026-06-14
Job specializations:
  • Insurance
    Risk Manager/Analyst, Insurance Analyst, Financial Analyst, Underwriter
Salary/Wage Range or Industry Benchmark: 80000 - 100000 CAD Yearly CAD 80000.00 100000.00 YEAR
Job Description & How to Apply Below

Job : 9920

Employment Type: Existing Role

Working Business Language: English. This role is considered a head-office role and will be required to communicate with internal and external stakeholders across Canada where the primary business language for this role is English. As such, the successful candidate must be fully proficient in English.

Salary: At Wawanesa, salary is only one component of a holistic, comprehensive and competitive offering that we provide to our employees. In addition to salary, full-time and part-time permanent employees are eligible for an annual bonus plan, leave of absence top-up programs and generous vacation time, personal days, premium free benefits and a pension plan. The salary offered for this role is determined with consideration to various factors, including but not limited to: your work location, local labour market conditions, external market salary data, internal pay equity and the knowledge, skills, experience and anticipated proficiency in the role.

The salary offered is estimated to be within the following range: $80,000 - $100,000. Candidates with salary expectations outside of the range are still encouraged to apply.

About Us

At Wawanesa, we offer a hybrid work environment that offers flexibility to our employees in balancing in-office (2 days per week OR 15 hours per week in a Wawanesa office) and remote work. You may work from any of the following locations:
Toronto (North York), ON;
Kitchener, ON;
Ottawa, ON;
Dartmouth, NS;
Moncton, NB.

The Wawanesa Mutual Insurance Company (“Wawanesa Mutual”), founded in 1896, is one of Canada’s largest mutual insurers, with over $3.5 billion in annual revenue and assets of $10 billion (CAD). Wawanesa Mutual, with its National Headquarters in Winnipeg, is the parent company of Wawanesa Life, which provides life insurance products and services throughout Canada, and Western Financial Group, which distributes personal and business insurance across Canada.

Wawanesa proudly serves more than 1.7 million members in Canada, and we are home to more than 3,300 employees distributed across the Canadian regions and communities where we operate. We give back to organizations that strengthen communities, donating more than $3.5 million annually to charitable organizations, including over $2 million annually in support of people on the front lines of climate change.

We are also proud to be recognized as one of Manitoba’s Top Employers. To learn more visit

We are currently looking for dedicated, driven, and enthusiastic individuals who thrive in an environment that welcomes change and are looking for an opportunity for diverse experience and advancement on a growing team.

Job Overview

Working under minimal supervision, the Senior Automobile Underwriting Midmarket Commercial Lines is responsible for analyzing the acceptability of complex and high premium volume business according to company guidelines by working collaboratively with our sales force and providing value added expertise and service to both potential and existing policyholders.

Job Responsibilities
  • Fleet & Garage Management and Analysis:
    You will be responsible for risk analysis using technology as well as external data sources for the purposes of quoting, negotiating and authorizing the acceptance of risk.
  • Knowledge Sharing:
    You will actively contribute to the team's ongoing training by sharing your knowledge and expertise to promote collective excellence.
  • Portfolio Development in Ontario & Maritimes:
    You will contribute to the strategic development of our portfolio in the Ontario & Maritimes region, working closely with our broker partners and internal stakeholders.
  • Rapidly Growing Region and Department:
    By joining a rapidly expanding department, you will benefit from personal and professional development opportunities while playing a key role in achieving business objectives.
  • Participation in Fleet Development:
    You will be involved in the evolution and management of the fleet for Wawanesa's Commercial Insurance department, directly contributing to our growth and success.
  • Networking and

    Collaboration:

    You will maintain excellent relationships with our broker partners, participating in industry events to exchange ideas and promote Wawanesa's expertise.
  • Pricing and Renewal Management:
    You will assess policy renewal eligibility according to the company's guidelines, while aiming to strengthen customer retention.
  • High-level customer service:
    Serve as a key point of contact, offering professional, expert, and proactive service.
Qualifications
  • Minimum of 5 years of Commercial Auto Underwriting Experience (Fleet & Garage)
  • Post-secondary education or related business experience
  • Completed or actively pursuing a Property and Casualty Industry Designation (e.g.: CIP)
  • Working knowledge of Microsoft Office Suite and underwriting software
  • Excellent attention to detail with the ability to review information carefully and comprehensively
  • Strong analytical and problem-solving skills with the ability to provide…
Position Requirements
10+ Years work experience
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